Hydrochloric Acid → HCID 19775705, compound

HRID 1613272Notes

Reaction equation

HRID 1613272 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.Cl>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([N:8]2[C:20](=[O:21])[C:19]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]3[C:17]2=[O:22])[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 19775705HCID 19775705, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.8 g (40 mmol) of 3,5-di-tert-butyl-4-hydroxyaniline and 5.9 g (40 mmol) of phthalic anhydride in 100 ml of tetrahydrofuran was refluxed for 24 hours. Concentrated hydrochloric acid (0.5 ml) was added and the mixture was refluxed for an additional seventeen hours and concentrated in vacuo. The resulting solid (13.2 g) was washed successively with water and hexane and then recrystallized from acetone-hexane to yield 10.9 g (31 mmol, 77%) of N-(3,5-di-tert-butyl-4-hydroxyphenyl)phthalimide, mp 196°-201° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe mixture was refluxed for an additional seventeen hours
  3. concentrationconcentrated in vacuo
  4. washThe resulting solid (13.2 g) was washed successively with water and hexane
  5. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-a0839aa2888140448a57c08bc404a6f7
Source dataset
uspto-grants-1993_03
Patent number
US05192791

Reaction notes

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